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octylamino-1 lactose

CAS No.: 91876-69-6
Formula: C20H39NO10
Molecular Weight: 453.52400
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What is octylamino-1 lactose

**Introduction to Octylamino-1 Lactose** Octylamino-1 lactose is a synthetic carbohydrate derivative where an octylamino group is introduced at the C-1 position of lactose. This modification enhances its amphiphilic properties, making it valuable in pharmaceutical and biochemical applications. The hydrophobic octyl chain improves membrane permeability, while the lactose moiety retains biocompatibility and targeting capabilities. Octylamino-1 lactose is particularly useful in drug delivery systems, acting as a carrier for hydrophobic drugs or as a ligand for lectin-mediated cellular uptake. Its unique structure also supports research in glycobiology, enabling studies on carbohydrate-protein interactions. With its balanced hydrophilicity and lipophilicity, octylamino-1 lactose offers versatile utility in therapeutics and diagnostics.

Preparation Process: To prepare octylamino-1 lactose, dissolve lactose (1 equiv.) in a mixture of water and methanol (1:1 v/v). Add sodium cyanoborohydride (1.2 equiv.) and adjust the pH to 6-7 with acetic acid. Introduce n-octylamine (1.5 equiv.) dropwise under stirring at room temperature. Monitor the reaction by TLC or HPLC. After 24-48 hours, quench the reaction with aqueous sodium bicarbonate and concentrate under reduced pressure. Purify the crude product by column chromatography (silica gel, eluent: CH₂Cl₂/MeOH 8:2) to isolate octylamino-1 lactose. Characterize the product by NMR and mass spectrometry.

Usage Scenarios: Octylamino-1 lactose is a synthetic derivative of lactose, where an octylamino group is introduced to enhance its properties. It is primarily used in biochemical and pharmaceutical research as a surfactant or stabilizing agent due to its amphiphilic nature. This compound can improve the solubility and delivery of hydrophobic drugs in aqueous systems, making it valuable in drug formulation. Additionally, it serves as a ligand or targeting moiety in glycoconjugate studies, aiding in cell-specific interactions. Its applications extend to nanotechnology, where it stabilizes nanoparticles and liposomes. In diagnostics, octylamino-1 lactose may assist in glycan-based assays or imaging probes.

octylamino-1 lactose Basic Info
Chemical Name octylamino-1 lactose
Synonyms (2S,3R,4S,5R,6R)-2-((2R,3S,4R,5R,6R)-4,5-Dihydroxy-2-hydroxymethyl-6-octylamino-tetrahydro-pyran-3-yloxy)-6-hydroxymethyl-tetrahydro-pyran-3,4,5-triol
CAS No. 91876-69-6
Molecular Formula C20H39NO10
Molecular Weight 453.52400
PSA 181.33000
LogP -2.04850
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